When Sam met Christian
by fluffmania207
Summary: Something odd is going on in Seattle, so the Winchesters make a stop in at Grey Enterprises Holdings Inc. to get to the bottom of the mystery. But the enigmatic and controlling CEO may be more than he appears.
1. Chapter 1

**When Sam met Christian**

 **A/N: It's been a while, but this fic needed to happen. For some context, I've been reading a sporking by Gehayi and Ket Makura of the Fifty Shades Trilogy. I am just over halfway through the spork of book 1, and I am categorically furious. I can't even read the entire deal in one go, because it makes me** _ **mad**_ **. For many reasons, but I will outline just three.  
1: Nobody deserves the treatment Ana receives. Not from anybody. She is uninformed, naive, and raped into submission by a total asshole with delusions of grandeur. Entering into any kind of deal you don't understand should be done carefully, and with a lot more research than just taking the word of a total douchenozzle.  
2: The sort of excrement portrayed in this book is not romance, it is not sexy, it is not okay. I had a PSA regarding stalking in one of my other fics, but I will tack one on here too. If a person behaves the way Christian Grey has behaved in this book, get help. Call the police. Report them. Man or woman, gay, lesbian, bi, cis, trans, or any other way you choose to live your life, you deserve to be loved, and treated with total and absolute respect.  
3: In the words of Imagine Dragons, "** _ **I'm fired up and tired of the way that things have been"**_ **. I'm tired of rape culture, and I just want to right this wrong, even if it means calling on three good – fictional – friends who have helped me through some serious, ahem, excrement.**

 **So, with that PSA out the way, let's dive in.**

Chapter 1

Sam Winchester adjusted the suit jacket, and ran his fingers through his hair. There had been reports of suspicious activity in Seattle, Washington, and Sam was on his way to interview one of the senior managers at Grey Enterprises Holdings Inc.

Dean had rolled his eyes at the name. "since when does a company need to tell us it's an enterprise, a holding, and incorporated?"

Sam had raised his eyebrows at that comment. Dean was not exactly known within the hunter community as being particularly hands on with the nitty gritty research. That comment would have surprised most hunters, but Dean was a man of many talents. "My guess, the guy who started the company, some guy named Christian Grey, thought the name sounded good, without looking deeper into the implications."

Sam now stood, looking up at the building in front of him. He really didn't want to go in. Sam hated corporate types, and he hated having to interview them even more. But this was necessary. Five young women had gone missing in the city over the last few months, and every single woman had been linked back to this company. They had all begun internships within the company, vanishing shortly after.

The reason the two hunters were even there was that most of the women had vanished from their apartments, with no sign of the doors or windows being forced. The local police had only found fur at the scenes, causing some speculation as to what was taking the women. And so, the hunters had decided to investigate.

Sam entered the large reception area, and made his way over to the desk along the far wall. A moderately attractive blonde woman smiled up at him, taking a quick look at the FBI badge he handed to her. "Agent James Morrison. You must be here to talk to Rebecca."

Sam nodded. "Which way do I go?"

The receptionist, Sienna Cole, handed him a visitor's pass. "Go to the elevators on the left. The security guard will direct you to her office."

Sam smiled, and followed the directions given. Dean was busy interviewing family and friends; otherwise he would have been with Sam, snarking at all of the bland beige décor. Somebody had clearly decided white was too stark, and any other colour was far too unprofessional. So here Sam was, inside a beige elevator with a security guard in an eggshell coloured jacket, and they were currently stepping out into a cream hallway.

Through one more set of glass doors later, Sam found himself in the waiting area of an executive office. The blonde assistant smiled at him, and offered him a seat. "Miss Kennedy will see you shortly, Agent Morrison."

Sam nodded, taking the cup of coffee he had been offered, and looking out over Seattle through the floor to ceiling glass window.

Ten minutes later, the phone on the assistant's desk buzzed. "Send in the FBI agent, Patricia."

Patricia stood up, and Sam stood with her. The door opened, and a brunette stood up from behind the desk. "Thank you, Patricia." She turned to Sam. "Shall we take a seat?"

Sam followed the woman to the set of cream-coloured armchairs in the corner, and fought a smile. But Rebecca Kennedy had already seen it. "Something amusing, Agent?"

Sam shook his head. "No, ma'am. Just noting the colour scheme. It seems a little…" he struggled to find the words.

Rebecca raised an eyebrow. "Beige? Because, trust me, it wouldn't be my first choice. But Mr Grey, he requested every office space and public access to be uniform and professional. Hence, the beige."

Sam smiled. "At least I don't need to work in the space full time." He picked up the manila folder he had been carrying. "You know why I'm here."

Rebecca nodded. "The women. The disappearances."

Sam nodded. "We have reason to believe they were all linked to the company."

Rebecca sat back. "Yes, they were all interns here at one point. But that is no reason to believe we are involved in the disappearances. The police have already looked into this."

Sam opened the folder. "With all due respect, we do need to conduct our own investigation."

Rebecca shook her head with a smile. "I know. It is just so frustrating, having so many police through the building."

Sam continued asking questions, establishing that the five women had all been interns to the top level managers; one had even been an intern for Rebecca herself. "Josephine had been such a hard-worker. Willing to go the extra mile. It was a loss to my department when she vanished."

Sam shut his notepad. He had been recording the conversation anyway, but had been taking notes regardless. "Can I get a copy of the security footage for the last three months? I'm interested to see if there was anything the women did that could have caused this."

Rebecca stood up and went to her desk. While she made the call to security, Sam looked out over the city. Someone or something in this city had taken those women, and it was up to him and his brother to find out what, and put a stop to it. Rebecca put the phone down. "Just wait here, Agent Morrison. The security department will bring the footage to my office once they have copied it.

XxxxxxxxxxxX

Sam rubbed his eyes, and pushed to his feet. He had been watching the security footage for close to five hours, and nothing interesting had happened yet. Dean was doing the same, but he had also drawn a blank. "Five hours, Sam. Five hours, and nothin'."

Sam grabbed a glass of water. The small motel was currently home, until the case was done. Until then, Dean and Sam were stuck here. Sam stared at the moose head on the wall, and frowned. "There's something we're missing, Dean."

Dean looked up. "It seems normal, aside from this place looking like the Stepford Wives. I swear only blondes work here."

Sam rolled his eyes. "Trust you to notice."

Dean grinned. "What can I say? I'm a man of taste." He then frowned. "But this is creepy. The people who are in the public eye – reception, assistants – they are all blonde. Interns are brunette. Everyone else is male."

Sam went over to where Dean was sitting. Dean had been reviewing the footage in the waiting area of the CEO, and Sam watched as the assistant moved about, printing and filing. A brunette entered, and Dean paused. "That woman? She's Marisol Olsen. The latest victim. This is a week before she disappeared. She was sent for by the CEO, that Grey guy, for a meeting. A week later? Gone."

Sam frowned. "Any other correlation? This could be a coincidence."

Dean raised an eyebrow. "Coincidence? Sammy, when have we ever believed in coincidence?"

Sam pulled a face. "Never."

Together, they began to track through the footage. Each time, a week before the disappearances, the woman in question had been called up to the CEO for a meeting. It was all far too convenient for Sam and Dean.

XxxxxxxxxxxX

Sam watched Dean take a bite of his greasy burger. "How can you eat that?"

Dean chewed loudly, and took another massive bite. He knew it irritated his brother. Sam was patient, waiting for Dean to finish being a child, and answer his question. Once Dean was done slurping his soda, he tossed the burger wrapper into the trashcan in the corner. "Sammy, I say we bust into that office, and go over it with EMF, Geiger counter. Something is in there that doesn't like women."

Sam nodded in agreement. It was time for action. Well, almost. It was still only around three in the afternoon, far too early for some breaking and entering.

As Dean stood up, a rush of cold static filled the room, accompanied by a loud pop. Both men turned to face their new arrival. The man stood there in the corner, his trench coat out of place anywhere else. But on Castiel, it was part of the package. "Cas, you made it."

Dean was pleased, and went over to give the angel a hug. Sam waved, and picked up his takeout container. He tossed it into the trash, while Dean filled Cas in on what had been going on. Cas, as always, was pretty impassive, but he listened anyway. Dean finished recapping what they had, and showed Cas the footage. "This office, you need to get into it?"

Sam shrugged. "Sure, it would be handy to know what's behind that door."

Dean pulled a face. "Probably more beige."

Cas looked at them both. He didn't understand the tone of Dean's voice, but he realised there was some joke he had missed. This was nothing new, really. He was used to being on the outside, looking in. "I can get you into the office."

Sam picked up his cell phone. "can you do it without blowing every electronic device in the building?"

Cas looked sheepish, but nodded. Dean grabbed his jacket, and picked up his own cell phone. It was times like these that Cas was definitely handy. Cas walked over to them. "Ready?"

Both men nodded, and then vanished.

XxxxxxxxxxxX

Christian Grey stood at his office window, looking out over early afternoon Seattle. He scowled at nothing, and turned away from the dazzling view. There was no real need for him to even be here, not when his board of directors usually managed a lot of the workload. This left the usually busy man at a loose end, especially since news had filtered up through the ranks that an FBI agent had visited his building, looking for information on some missing interns.

Grey sat down in his executive chair, and fidgeted with a pen, before he pushed to his feet. He needed air, and he needed to burn off some excess energy. He pulled the inter-leading door between his office and the waiting area open, and walked past his assistant without a word. He didn't need to answer to her. He answered to nobody.

Grey strode through the hallways, and up a small flight of stairs. His destination was the small rooftop seating area, its primary function to allow meetings to be held in the open air, and away from prying eyes and video cameras.

The afternoon sun streamed around him, and Grey stared off at the cityscape. A slight static charge made him jump, and he looked around. Nothing. Grey shrugged. It had clearly been a long day, and he was now imagining things. He stayed where he was, enjoying the sunshine, unaware of what was going on below.

 **A/N2: So, I hope you enjoyed the first instalment. Any feedback would be helpful, and reviews always make me smile. See you next chapter.**


	2. Chapter 2

**When Sam met Christian**

 **A/N: Thank you to those who have read the last chapter. I feel it pertinent to point out that I'm attempting to portray everybody as accurately as possible. This is difficult, however, when dealing with Fifty Shades, where we were told one thing, but saw another. So, I'm going to try and write Ana Steele and Christian Grey as EL James intended to. Wish me luck, since I don't have much from the source material.**

 **I hope you stick with me to the end. Here's the next instalment…**

Chapter 2

Den shoved the EMF reader back into his pocket, and scowled. "No EMF, and no strange cold spots. This place is clean."

Sam glanced at Cas. "Anything?"

Cas shook his head. "There are no signs of demons or angels here, Sam."

Sam shoved his hands into his pockets. The office was large, and a typical CEO office space, and the expected beige. What did stand out was the large glass desk, devoid of any paperwork. This CEO obviously had a good board of directors, which clearly handled a lot of his work. Cas tilted his head. "The occupant of this office is returning."

The brothers rushed to Cas' side, and vanished out of the office space as the door began to open. They reappeared moments later in their motel, and Dean shook his head. "There's nothing living in that office. Whatever it is, that isn't the place to find it."

Sam rolled his shoulders. Something was still off about the whole deal. Call it hunter instincts, but Sam was not satisfied. And he didn't think Dean would be either. His brother slumped down on the edge of the bed. "Sammy, this whole thing stinks."

Cas walked to where the footage was paused on the computer screen. "Maybe you should meet this human, Christian Grey. He might be the source of the trouble."

Dean turned to Cas. "That would explain the lack of activity."

Sam shrugged. "It's an explanation. We can set the meeting up for later in the week."

While Sam made the call to Jessica to arrange a meeting, Dean grabbed a beer. He refused to give one to Cas. The angel had no limit to how much alcohol he could stomach, and Dean wanted to have some beer left, dammit. As Dean took a swig, his gaze lighted upon the newspaper clippings on the far wall. The faces of five women peered back at him, and frowned. "Sammy, do these women look similar?"

Sam slid his phone back into his pocket, and moved up next to his brother. His brow furrowed. "They do, kinda."

Dean took another sip of beer. "Like a serial killer. This thing must have a specific type."

Sam shook his head. "We have a meeting with Grey scheduled for tomorrow afternoon."

Dean scowled. "Do I have to wear a suit?"

Sam shrugged. "Probably. The dude seems like a real corporate shark. Probably expects it."

Dean rolled his eyes, but said nothing. Well, except to mutter under his breath, "Great, more corporate sharks."

Sam hid his grin. Dean wasn't exactly sold on corporate bastards, not since the angels had attempted to use them to start the Apocalypse. So, this meeting with a CEO could be very interesting.

XxxxxxxxxxxX

Dean raised an eyebrow as they entered the elevator. It was just him and Sam, with Cas needed elsewhere. He had promised to return at a later stage. Right now, Dean was quietly mocking the décor. He leant over to his brother. "I thought you were exaggerating. The décor is really this bland?"

Sam smiled. "Yeah, it's this bad all the way through the building."

Dean pinched the bridge of his nose, squeezing his eyes shut. "Let's just get this over and done with, so I can get out of this monkey suit."

The elevator came to a stop, and the door slid smoothly open, revealing more beige carpet, and an impressive view of Seattle. But neither of those things held the attention of the hunters. What held their attention was the fact that they had almost been bowled over by a fleeing figure. Small, with dark hair and large blue eyes, the woman almost tripped over Dean in her effort to leave the waiting area. Her eyes held real fear, and Dean went for his gun. There must be something here to scare this woman that badly.

The Winchesters were on alert, but there didn't seem to be any threat, if you didn't count the man in the black suit standing in the office doorway, glaring at the elevator doors as they slid shut. Sam nudged his brother, who straightened his suit jacket, returning his gun to his holster. The man was obviously the CEO, and moderately famous businessman Christian Grey. Sam's first thought probably mirrored Dean's; _"I thought he'd be taller."_

Maybe it was just the Winchesters being vain, but Grey seemed surprised to see the two hunters in his office. He looked away from the elevator, and mimicked Dean's move of straightening his suit. His grey tie mirrored his grey eyes, and Sam fought to keep his expression neutral. The man was like a walking embodiment of his own décor; bland and stark.

Grey looked them over. "You must be the FBI agents. Please come in."

XxxxxxxxxxxX

Grey sat in the largest armchair in his office, casually crossing his left ankle over his right knee. The two agents stared at him, and Grey tried not to shift uncomfortably in his seat. As a man so used to being in his own space, and being in charge of everything, it unnerved him that the disquieting stares of just two agents could make him nervous.

The taller agent – Morrison – picked up the folder he had been holding. "We had some questions, Mr Grey, about the five women who have gone missing in the last three months. All of them had this company listed as their last place of employment."

Grey shrugged. "Coincidence. Lots of people work for my company."

The other agent, William Gibbons, leant forwards. "How many of those people disappear without a trace?"

Grey levelled his gaze on the other man. "Those disappearances have nothing to do with Grey Enterprises Holdings Inc."

Agent Morrison glanced back at the folder. "We were able to confirm each intern met with you at least a week before disappearing. We'd like to know what was discussed."

Grey rested his elbow on the arm of the chair, his chin on his hand. "I'm not sure I can share that information."

Agent Gibbons rested both elbows on his knees, and pulled a slight face. "You're saying you met with them, and they just happened to disappear a week later, with no coincidence? Even though they worked for your company and were productive members of the community up to that point?"

Grey didn't move. These men, they didn't know what they were getting into. Sometimes, it was better not to ask questions. "I think it would be better for you both if you leave now. You've said far too much already."

XxxxxxxxxxxX

Sam stretched, rolling his shoulders to ease the cramping. "This Christian Grey is definitely an odd character."

Dean sat up. He had been lying on his bed, trying to sleep. But Sam had been insistent. He rubbed his eyes. "Sammy, please. It's late. I need some sleep."

Sam scowled. "Dean, this is pretty important. This Grey guy, there's something not right about him."

The older Winchester muttered under his breath, but pushed to his feet and came to lean over his younger brother's shoulder. In the many windows Sam had opened, there was an image search of Christian Grey. Dean scanned the pictures. "What's wrong? No black smoke, balls of light, strange images. What are you showing me? This dude is perfectly normal."

Sam smiled. "Good looking rich guy like him, and not a single woman?"

Dean looked again, and frowned at the screen. "Son of a bitch. You're right."

A rush of static startled them both, and they turned to look at Cas. The angel looked back at them. "Hello, Dean, Sam."

Dean straightened. They hadn't expected Castiel back so soon. "Anything you need?"

Cas shook his head. "I have information about your latest case."

Sam stood up. "Breaking and entering, Castiel?"

Cas didn't react to the subtle jibe. "I managed to access the residence of this Christian Grey. And I think you need to see this."

Dean picked up his jacket. Sam grabbed his phone, and a large duffel bag that had been sitting at the foot of the bed. They didn't know what they were dealing with, so it was best to be prepared. The brothers looked at each other, and then at Cas. Cas nodded once, and the room vanished from around them.

Less than a second later, they were standing on a flat rooftop, next to a helipad.

XxxxxxxxxxxX

Grey stood at his window, hands in pockets, glaring off into the night. That girl, Anastasia Steele, was supposed to be here half an hour ago, but she was late. It must be that damn car she was driving. That death-trap was not safe for her. Grey needed to replace her car with something safer and far better suited to her future position in his life.

Jason Taylor, his bodyguard, stood next to the front door, not saying anything. Taylor wasn't known to be a talker, which Grey preferred. He had no inclination to get to know any employees beyond a professional setting. Taylor knew more than most, but that was a hazard of what Grey did in his spare time. He honestly didn't care what Taylor got up to, as long as the man was on time for work.

The phone rang, and Grey answered it. "She's here? Send her up."

Taylor opened the door, and vanished, leaving Grey alone with his thoughts. As he stood waiting for Ana and Taylor to arrive, Grey thought about the odd meeting he had been in earlier that day. The FBI agents didn't seem like the usual stuffy law enforcement he had met with before.

The shorter one had a haunted look in his eyes, like he had seen some serious shit; shit that gave you nightmares for the rest of your life. The taller one looked like a soldier, and reminded grey of the way Taylor would examine a room in a heartbeat for threats. He was almost overly attentive to his surroundings, a hair away from going postal. That must have been what unsettled him about them.

The agents had unnerved Grey, and he didn't like feeling off kilter. He just couldn't put his finger on why the two men had left him feeling intimidated, not when he was obviously superior to them. He certainly wasn't unnerved because they had so effortlessly made him feel inferior. That would imply he wasn't superior, and he definitely was-

That train of thought was quickly lost when that same static charge rushed through him. _Great,_ he rubbed his face. Now he was hallucinating at home too.

Maybe he needed a good sleep. He would have one once he was done with Ana and her tardy ways. She needed to learn her lesson about defying him. Especially if she wanted to have a place in his life.

XxxxxxxxxxxX

Dean took in the surrounds. Tall buildings and apartments as far as they could see. They were clearly in a city, on top of a high end apartment building. Sam moved towards the doorway that allowed access to the roof, and gently pushed it open. The stairwell was dark and empty, and the hunters moved through it with guns drawn. They definitely weren't taking chances.

Cas followed, seemingly oblivious to the fact that they were supposed to be sneaking. Sometimes the angel was terrible to sneak into places with. He had no concept of personal space, and his internal filter was nonexistent. This wasn't usually a problem, except to make life interesting. Dean grabbed Cas, pulling him to the edge of the stairwell.

Cas nodded, and they continued down do the next level. Dean made a complaint under his breath. "How much beige can one person take?"

Sam rolled his eyes, and the three of them continued down the hallway. The door ahead of them was shut, but they could hear loud voices on the other side of it. They sidled up to the door, and pressed themselves to the wall outside.

"Explain why you are late, Ana." That was Grey.

"I was having dinner with Kate. I can't be at your beck and call, Christian." A defiant female voice made Sam raise his eyebrows.

A hard slapping sound and a feminine cry of pain had Dean clenching his fists. "You will address me as Sir, or Mr Grey. Understood?"

The Winchesters didn't bother waiting for the reply. Sam stepped back, and delivered a solid kick to the door lock. The front door buckled, and then flung violently inwards.

 **A/N2: Please drop me a review, and tell me what you think. See y'all next time!**


	3. Chapter 3

When Sam met Christian

 **A/N: I have been reading a Stephen King novel called** _ **Gerald's Game**_ **, and it has given me some inspiration. If you want a psychological thriller that gives what Ana's reaction should have been, I suggest reading it. I trust a lot of you are enjoying this story. It's been cathartic. Thank you for sticking with me, and I hope you enjoy the next chapter.**

The scene was frozen in front of them. Grey stood over the same woman who had nearly run them over earlier that day, his hand raised above his shoulder. The woman – he had called her Ana – was clutching her cheek, an expression of shock on her face. A third figure stood in the corner, simply watching the scene unfold. He was the only one who reacted to the entrance of the two hunters.

He pulled out his gun, and aimed at the two men. The hunters froze in the doorway, Dean with his gun trained on Grey, Sam with his on the bodyguard. Grey looked up, and his jaw almost dropped in surprise. He stepped away from Ana, dropping his hand. "You."

The word was low, a growl, but it made Ana jump back in surprise, her breath hitching from what the brothers guessed was fear. Sam noted the tears in her eyes, and that just enraged him further.

"Like hitting women, _Christian_?"

The snarky comment came from Dean, who was just as livid as his brother. Grey lifted his hands, and smiled. It was a shark's smile, or that of a snake before it bit you. "I didn't think you were FBI." He gestured with his hands still in the air. "So what are you? CIA? Special Forces? Are you even cops?"

Sam didn't move. He kept his gun pointed at the bodyguard, who was busy aiming his own gun at Dean's head. "Does it matter?"

Grey rolled his eyes, and looked away at his bodyguard. "Taylor, shoot them."

The brothers stood their ground. Ana stood in the middle of the room, quietly sobbing. Neither of the brothers could risk going to her without risking getting shot. They were at a stalemate, and Grey began to laugh. "I see. You come bursting into my house, with the intention of shooting me, and now neither of you has the balls to do so. Some cops you are." The scorn in his voice was evident, and it grated against Dean's senses.

Taylor kept his gun on the bigger threat, Dean, but kept his eye on Sam. No sense in letting either of the men get the upper hand. Ana continued to sob, and flinched slightly when Grey moved his right hand impatiently. Frankly, she deserved another slap, in Taylor's opinion. She had been too disrespectful with Mr Grey, and she needed another lesson from him.

The mood of the room suddenly changed; Grey suddenly stood still, his eyes wide in surprise. Sam could predict why. Castiel now stood between the brothers, impassively taking in the scene. Grey eyed the angel out, clearly not comfortable in his presence.

Few people were. The brothers were used to the unease – either that, or they had killed so many evil bastards, one confused angel was hardly going to set their instincts off. But Grey and his henchman were clearly unnerved by the way the angel regarded them with the same impassivity one would use to look at a particularly dull spreadsheet.

Cas looked at the three figures in the room, and his eyes lighted on Taylor, who looked like he had just seen a ghost. He appeared physically repulsed by Cas, and he fought to stay in place. "He is not-" before Cas could finish, he tilted his head, listening to heavenly orders. "I need to go."

With the now familiar static pop, he was gone. Grey blinked, swore, and then looked at Sam and Dean. "Who are you guys?"

Dean didn't move, his gun trained on Grey. "Your worst nightmare, in your living room."

Taylor grinned, and then began to laugh. "I think we have that covered, Dean Winchester."

Sam kept his own gun on Taylor, and managed to hide his surprise. Grey, however, couldn't. "You know these people? Are they friends of yours?"

Taylor grinned, and shook his head. "No. But they are pretty well known in the hunter community." He looked at the brothers again. "I didn't think it was you guys, until that damn angel appeared. Only two hunters travel with one of them bastards, and you're it."

Sam pulled the trigger, and Taylor jerked like he had been shot. But he didn't move. Ana's eyes were bugging out, and Grey grabbed her arm to drag her out of the way. Sam fired again, but it was clear bullets were doing very little to slow the bodyguard down. There was a loud tearing noise, and Taylor convulsed on his feet. His clothing disintegrated, and fur began to sprout from underneath his skin. Dean backed up to Sam. "Skinwalker? Son of a bitch."

Sam nodded, his face grim as he holstered his gun. "Got any silver?"

Dean pulled out a knife, and nodded to his brother. The skinwalker launched at Dean, who put his arms up to defend himself. There was a brutal scuffle, and Sam pulled out the blade used to kill demons. It wasn't made of silver, but it would still hurt.

Sam lunged into the fray, the two brothers fighting against a brutal opponent. The goal was to incapacitate or kill, without being bitten. Sam and Dean had Taylor backed into the corner, each of them brandishing a knife, when Sam realised they had forgotten about the other threat in the room. But he couldn't take his eyes off of the skinwalker in front of them.

A hard knock on the back of Sam's head had him pitching forwards. He was vaguely aware of Grey standing over him brandishing a large stone sculpture, before the world faded to black.

XxxxxxxxxxxX

Grey paced across the locked bathroom door. Ana was having a woman moment, throwing up from the scene she had just witnessed. Grey didn't care how weak her stomach was. He just wanted to make sure she wasn't messing up his bathroom. Grey glared at the closed bathroom door. This was the problem with women; too weak for this world. This was why they needed to be coddled and protected and taught to tow the line.

Taylor appeared from upstairs, pulling on a t-shirt. His clothing had been destroyed in his transformation. "They secure?"

Taylor nodded. "They're ready for you, Mr Grey."

Grey grinned, and started for the stairs. He paused. "Make sure Anastasia hasn't ruined my bathroom completely."

Grey didn't wait to see if the order had been followed. He stalked up the stairs, and into what he affectionately referred to as 'The Playroom'. The playroom was where he kept all of his fun stuff. Shackles, ropes, cable ties, ball gags, clamps, whips, canes, and other items that he used to have his fun. The press would have a field day if they ever found out about this place. Because conservative, wealthy men were not meant to be into beating their partners for pleasure.

But this wasn't about pleasure. This was about punishing the hunters. The word seemed strange to Grey, but Taylor had been adamant that these men were a threat. Grey felt the anticipation build as he saw the shorter man – Taylor had called him 'Dean' – shackled to the St Andrew's Cross in the centre of the room. He was wearing just his jeans and a t-shirt, having been stripped of his jacket, shoes, and weapons by Taylor. Dean was awake, and alert, but surprisingly impassive. "This is what gets you off? Or do _you_ prefer to be strapped to this thing?"

Grey scowled. "I don't tolerate that sort of talk in here, Dean."

Grey could see the other one – he couldn't remember the man's name – shackled to the bed in the corner. He was only just starting to come around. Dean craned his neck, his concern for the other man apparent. "Sam! Sammy! You okay?"

Sam moaned, and Dean breathed an obvious sigh of relief. And then he fixed his gaze on Grey, who was now standing in front of him. Those haunted green eyes startled Grey, who hid his surprise behind a sneer. "You can't do anything to me that I haven't experienced before, Christian."

 _Sam._ Grey grinned. "Would you prefer Sam was on that cross instead?"

He picked up a cane as he spoke, but Dean didn't flinch. He didn't even take his eyes off the billionaire, which was a little unnerving.

Grey grinned. "It's good for you that I didn't get Taylor to strip you completely. Because this will hurt."

Dean rolled his eyes. "Is that what that monster calls himself? Because we hunt bastards like him. And we're damn good at it too."

Grey brandished the cane. "Don't get too cocky, Dean. I don't like cocky."

He brought the cane down across Dean's thigh, and grinned when Dean winced slightly. This was definitely going to be fun.

XxxxxxxxxxxX

Sam was jolted awake by a loud _thwack_ , and tried to sit up. Something stopped his arms from moving, and he turned his head to see what it was. Shackles bound him to a bedpost. On both sides. Great. Sam heard a second crack, like a whip, and strained to see what it was.

The seasoned hunter got a fright when he realised his brother was tied to some torture device, and Grey was in the process of hitting him with a cane. Dean, to his credit, didn't react beyond the occasional flinch. But that information didn't exactly settle Sam's stomach. Not when he knew Dean often woke during the night in a cold sweat, the name _Alistair_ on the tip of his tongue.

Dean's four months of actual Hell had left an impact, but Sam didn't want his brother to suffer any further. "Hey! Asshole! Why not pick on someone your own size?"

Grey froze, and turned to face Sam. "I'm coming to you next, Sammy. Don't you worry." He gestured at Dean, who was glaring at him and attempting to hide how much his ribs were hurting. "First, I need to teach your friend here why I'm the one in charge."

Sam laughed scornfully. "Yeah, you're totally the one in charge, since you get your rocks off on beating innocent women. I'll bet those disappearances were you taking things too far, and your skinwalker pet finishing the job."

Grey began to change colour at the jibe from Sam. In any other circumstance, it would have been humorous to watch a man change from pale to bright red to pale in the space of thirty seconds. As it was, Sam was concerned the man was about to pass out. Grey seemed to get his temper under control, and tried for a casual grin. It seemed forced, fake. "I see you've been doing your research, Sam."

He swung the cane out wide, narrowly missing the side of Dean's head with the tip. Dean ducked out of the way, as much as he could. "Son of a bitch."

Grey didn't stop. "But, I'm the one in charge here, so we play by my rules now."

Sam rolled his eyes. He was baiting the man, but he wanted the billionaire CEO to lash out, because angry men made mistakes. "You're only in charge when your subjects can't move? How quaint. Let me go, and then we can go head to head. Let's do this for real, _Christian._ "

Dean struggled against his shackled, the chains clattering against the wood of the cross. "Sammy, no! Just leave it. I'm fine."

Before Sam could reply, the door to the shitty porn hellscape cracked open. "She's ready, Mr Grey."

Grey smiled – a real smile – and turned to the door. "Send her in, Taylor."

The door opened fully, and Sam strained from his position on the bed to see who had just entered. Ana stood in the doorway, the shock on her face clear as she tried to process what she was seeing. Sam couldn't blame her. Nobody deserved to be thrown into such a strange mess with no warning. But she didn't seem to be shaking, just looking at everything and figuring out what was going on.

To her credit, she seemed to be handling it better than he would have expected. She took in the room, and eventually looked at Dean, still struggling against the shackles. "What are you doing to him?" Her voice was soft, and cracked right at the end.

 _Perhaps she's not holding up like I thought_. Sam yanked hard on his left hand, while Grey turned away, gesturing in Dean's direction. "I'm teaching Dean that it's impolite to burst into somebody's house with the intention to kill them. Especially when they have such lovely company."

He reached out, running the back of his hand slowly down her face. Ana jerked away from his caress, and Grey scowled. "Get her out of here!" yelled Dean, cutting into what Grey must have assumed was a romantic moment.

Grey swung to face him. "I'm in charge, Dean. My playroom. My rules. Now, stay there like the good captive you are, and let me use you to teach Ana what happens when people disobey me."

Ana surreptitiously sidled away from the billionaire, but Grey was no longer focussed on her. He regarded Dean with contempt – actual contempt – before pulling out the knife Sam had been carrying. Both brothers swore, and Ana jumped, backing away further. That wasn't any ordinary knife. It was a demon-killing knife. And now Grey was brandishing it like some swashbuckling pirate.

Grey grabbed the front of Dean's t-shirt, and sliced it open right down the middle. "There, now you're ready to receive your punishment."

Dean didn't react, and Sam yanked on his right shackle. He yanked hard, and felt something give. The bed setup, while perfect for whatever perverted ideas passed for fun around here, was not meant to actually restrain an unwilling victim. And Sam was definitely unwilling. He yanked again, and the screws holding the shackle to the bed broke free. Grey froze. Ana realised what had happened, and pushed over a pile of sex toys to cover the noise of breaking screws. She wanted Sam free, because this Christian Grey was a maniac.

Grey swung around, and stalked over to her. He loomed over her like a menacing black shadow, and the timid woman shrunk under his penetrating gaze. "Anastasia, go and stand over there in that corner, and don't touch anything. You cannot interrupt my work again."

Ana nodded meekly, and slunk into the corner. Sam caught her eye, and nodded his thanks. Ana merely tipped her head, and then looked away. She appeared to have locked eyes with Dean, offering him what little support she could.

Sam slowly sat up, and gripped his left wrist in his right hand. As much as it disgusted him, he could use the beating Dean was receiving to his advantage. As Grey brought the cane across Dean's chest, yelling obscenities as he did, Sam yanked on the shackle. Dean was watching out of the corner of his eye, and silently approving. Even though he thought the whole idea of a beating really distasteful.

It took three pulls for the shackle to break free, and Sam pushed off the bed in one movement. He grabbed what he assumed was a whip, and then put it back. This called for some real, hand to hand beating. As Grey brought the cane up for another strike, Sam grabbed his arm from behind. Grey ended up flat on his back, winded and trying to draw breath. Sam grinned. This was going to be good.

 **A/N2: I tried to make Grey sympathetic, I really did. But I had a serious case of the character fighting against what I wanted. It happens sometimes. Please leave me a review, and let me know how I'm doing. There will probably be one more chapter, and an epilogue, but that could change once I write it. Thanks again, and see y'all next time.**


	4. Chapter 4

When Sam Met Christian

 **A/N: Sorry this has taken so long. I have some exams coming up, but I took some time to finish this off. It was basically complete. This will be the last chapter, with an Epilogue at the end. Thank you for joining me on this journey. It's been fun.**

Chapter four

Dean watched helplessly as his brother fought off the billionaire. It was times like these that Dean was known to stress endlessly about his younger brother. But his main concern was Ana. The woman was frozen on the other side of the room, clearly shocked at what had been happening. Dean didn't exactly blame her. It wasn't easy being thrown into this room, immediately after finding out monsters were real.

Sam was holding his own; Grey was fit, but Sam was more practiced at defending himself. What Dean really needed to do was get off this cross, so he could go and find Taylor before it was too late. He tried to do what Sam had done, but the cross wouldn't budge. Dean pulled harder, and noticed the keys hooked on the wall next to the door. "Son of a bitch."

Grey was fighting back hard, but Sam wasn't budging an inch. Ana was gone from where she had been frozen, and Dean looked around wildly for her. A hand on his left wrist made him jump, and Dean turned his head to see Ana. She was holding the keys, and fumbled them as she tried to unlock Dean's arm.

Dean heard the lock click, and yanked his arm out of the shackle. He snatched the keys from Ana, and unlocked his right wrist. As he bent down to unlock his ankles, the door was flung open. Taylor stood in the doorway, glaring angrily at Sam and Grey as they traded blows. He shuddered, and an inhuman growl came from him as he tensed up ready to defend his boss from Sam.

Ana lurched towards the knives Sam and Dean had been carrying, and sheer luck had her grabbing the silver one. As Taylor lunged towards Sam, Ana followed suit. Dean finished unlocking his shackles, and scooped up the demon killing knife. He passed Ana, and wrapped his arms around Taylor's chest, jerking him back. He managed to wrestle Taylor away from Sam, who was half an inch from losing his jugular.

As he pinned Taylor down, his arms wrapped around Taylor's neck, Ana plunged the knife through Taylor's heart. The entire room froze as Taylor screamed, and then slumped in Dean's grip. Ana was shaking, and she stared in horror at her hands, backing away from Taylor. Dean could see she was going to go hysterical, and dropped Taylor. Dean tugged Ana's arm, and pulled her to her feet. "Shh," he wrapped his arms around her and tugged her away. She was curled against his chest, taking deep breaths and gripping the shreds of his shirt. "Shh, it's okay. He's dead. You're okay."

Dean watched over her head as Sam pushed to his feet. Blood was trickling from a cut on his eye, and there was blood coming from his upper lip, where Dean figured his lip had been split. Sam glanced back at Dean, who nodded once.

XxxxxxxxxxxX

Sam stood, breathing heavily. Grey was on his back on the floor, his face ashen from what Sam knew was a broken shoulder. Sam clutched the cane Grey had been beating Dean with, and flexed it between his hands. "You're only strong when your victim is handicapped." Sam spat some blood out onto the floor, and rubbed the back of his arm across his mouth. Blood smeared across his cheek. "But like this, one on one, you turn into a coward."

Sam threw the cane into the corner of the room, and advanced on Grey, who attempted to scrabble backwards, his fingers slipping on the polished floor. He wasn't getting very far with a broken shoulder.

The billionaire ended up trapped between a line of chain, and some leather straps, and Sam could see his hands were shaking. He pulled a face. "Beating you is like beating a child. You don't have the maturity to handle this. You never grew up."

Grey blanched, and his hands trembled violently as he ran his good hand through his hair. Sam turned slightly, and saw Dean holding Ana tight. She seemed to be shaking quite badly, but holding up otherwise. Sam walked to where he had discarded the cane, and picked it up. Grey pushed himself further into the wall, but Sam just shook his head. "I have no use to beat people like you." He returned the cane to the rack.

With one final glance at the whimpering man in the corner, Sam strode past Dean and Ana, and pulled the silver knife from Taylor's body. Dean pulled Ana with them. There was no way she was staying here.

Ana resisted Dean's pull, and turned to look down at Grey. He slowly uncurled himself and sat up. His bloodied lip was beginning to swell, and blood was pouring from his broken nose. "Ana, wait." The words were slurred around broken teeth and bleeding lips.

Ana pulled out of Dean's grip. She trembled, but stood strong beside the hunter. "Why, so you can hit me again? So you can prove how dominant you are?" Ana pushed her hair back out of her face, her expression resolute. "These guys are right. You're a coward. I'm going home."

Grey looked lost, but said nothing else as Ana pushed past Sam out into the hallway. She nearly stumbled into a third person, her fall prevented by the iron grip of Castiel. Dean nodded to Cas, who let go of Ana. "Are you okay?" the angel wore a largely blank expression, but Dean knew he was quite concerned for his friends.

Dean glanced at Sam, who looked at Ana. "We are."

Sam then turned to Grey. "You have some choices to make. We won't kill you now, but we could have. Become a better person, or we come back and finish the job. Clear?"

Grey nodded, and watched despondently as they left the playroom. One last look from Castiel, and the two hunters were gone.

Ana picked up her purse from the living room. She needed to drive home, but wasn't sure how she would. A strong hand closed over her arm, and she looked up at the other hunter, Sam. "Are you really okay?"

Ana nodded, although she wasn't sure it was the truth. "I need to get home."

Sam turned to Dean, who was in the process of pulling his jacket over the tattered remains of his t-shirt. They shared the sort of look that comes from a lifetime of working with a person, before Dean nodded. "We'll make sure you get home okay."

In the underground parking garage, Ana stood next to her car. The shock of the last few minutes was beginning to set in, and her knees were shaking. Ana tried not to think about the knife, or the way she had taken a life, but that wasn't easy. She wasn't a violent person, and the exposure to so much in one go had been a shock to the system. The hunters were with her, and they seemed to be arguing. Eventually, Sam came up next to her. "Want me to drive you home?"

Ana nodded, and fumbled in her pocket for her keys. Sam took them, and skilfully manoeuvred Wanda out of the spot she had chosen. Dean opened the passenger door for her, and helped her crawl into the back seat. He climbed into the car, and Sam drove to the exit. It was time to go home.

At her apartment, Ana let the two men – Sam had told her that they were brothers – in for some beers. To be honest, she just wanted to make sure she wasn't going to have a breakdown. Castiel was already there, but since Ana had watched the man vanish before her eyes, she wasn't surprised. Either that, or nothing could shock her anymore.

Dean made sure Cas – it was impossible, but he was apparently an _angel_ – didn't get beer, pointing out that the man had once drunk an entire liquor store's worth of alcohol, and only come back slightly tipsy. Ana really didn't want to lose her good drink on Cas. Not when she could possibly need it.

As they sat in the spacious room, Sam explained what it was they did. "So, you hunt monsters?" Ana was somewhat incredulous, but she had seen how unflappable the hunters had seemed in the face of danger.

Sam nodded, but Dean broke in. "We save lives. We stop things like Taylor from killing innocent people."

Ana took a sip of her beer. "You're heroes."

Dean looked down at his bottle. "Thanks."

Ana smiled at both of them, an idea occurring to her. "Need any help? Because I really don't want to go into the corporate world if it's full of people like him." She was taking a big gamble, but she also knew that Grey could have her kicked out of any corporation if he wanted. He had the connections.

She shuddered, and the brothers looked at each other. Sam raised an eyebrow and pulled a face, Dean mimicking him. "I think we know a guy who could use some extra help. How good are you at research?"

Ana grinned. "Top of my class at WSU for my English major, with Cum Laude in historical texts and documents. Does that help?"

Sam grinned, and pulled out a ratty business card. "When you're ready, contact this number. Ask for Bobby, tell him Sam and Dean sent you."

Ana took the number, and felt a fundamental shift inside her. She was home.

 _ **Epilogue**_

Early the next morning, an anonymous tip-off to the Seattle Police Department had the police and FBI raiding Christian Grey's penthouse suite. Grey himself wasn't there, but the police found enough evidence to conclude that Grey was a person on interest in the missing persons cases.

Grey Enterprises Holdings Inc. suddenly announced later that day that it was becoming a non-profit organisation, and that it was donating a large portion of its funding to local shelters for abused women. No reason was given to investors, beyond a generic letter that was distributed to the shareholders, employees, and the press.

The founder and CEO himself, Christian Grey, virtually disappeared. He left only paperwork detailing the shift to NPO status, as well as instructions that he was on an extended vacation. The police found all of this suspicious, especially since his residence had shown signs of a recent altercation. An extensive search was conducted, but Grey did not resurface.

Castiel eventually tracked Christian Grey to the south west coast of Mexico, where he was hiding out on a deserted beach, away from society. He was almost constantly drunk, and he didn't recognise the angel. Castiel figured he would leave the man to wallow in his misery, a victim of the circumstance he created.

Sam and Dean moved onto the next town, sure the threat was gone from Seattle. They kept in contact with Ana, who invited them to her graduation a few weeks later. Both of the brothers, as well as a bemused Castiel, attended.

Taylor was buried in an unmarked lot, with just a rock as a headstone. He left behind a daughter, who had no knowledge of her father, and did not know of his untimely passing.

After her graduation, Anastasia Steele called the number, and moved to Sioux Falls, South Dakota, to Singer Salvage Yard. After a little training from Bobby Singer, and learning some extinct languages, she became an invaluable asset to a lot of hunters looking for information. She could often be found sharing a beer with Bobby, Sam and Dean. Anastasia found her calling, and refused to think about the time she almost sold herself to a billionaire.

 **A/N2: Thank you for joining me on this journey. It's been interesting, and I have enjoyed writing this. Please drop me a review, and tell me what you think.**

 **Thanks again**

 **Until next time**

 **SJ**


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